2-Aminooxazole → 9H-Thioxanthene-9-carboxylic acid oxazol-2-ylamide

HRID 991212Notes

Reaction equation

HRID 991212 reaction equation
[NH2:1][C:2]1[O:3][CH:4]=[CH:5][N:6]=1.[CH:7]1[C:20]2[CH:19]([C:21](Cl)=[O:22])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[S:12][C:11]=2[CH:10]=[CH:9][CH:8]=1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[O:3]1[CH:4]=[CH:5][N:6]=[C:2]1[NH:1][C:21]([CH:19]1[C:20]2[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=2[S:12][C:13]2[C:18]1=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:22]

Participants

5

Reactant 2

HCID 5585212-AminooxazoleHCID 125156589H-Thioxanthene-9-carbonyl chloride

Product 1

HCID 539127719H-Thioxanthene-9-carboxylic acid oxazol-2-ylamideYield 18.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a stirred solution of (0.048 g, 0.575 mmol) 2-amino-oxazole [Cockerill & al., Synthesis 591(1976)], and DMAP (0.003 g, 0.03 mmol) in pyridine (2 ml) was added at 0° C. (0.100 g, 0.384 mmol) 9H-thioxanthene-9-carbonyl chloride. Stirring was continued at RT for 16 h, the reaction mixture was evaporated and water (5 ml)/sat. NaHCO3 solution (2 ml) was added. The solid was filtered off, dissolved in dichloromethane, dried (MgSO4), and concentrated in vaccuo. The crude material was purified by column chromatobraphy on silica gel (methylene chloride/ methanol 40:1) to give the product (0.022 g, 18%) as a white solid, m.p. 188-191° C. and MS: m/e=309.1 (M+H+).

Workup

  1. customthe reaction mixture was evaporated
  2. additionNaHCO3 solution (2 ml) was added
  3. filtrationThe solid was filtered off
  4. dissolutiondissolved in dichloromethane
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vaccuo
  7. customThe crude material was purified by column chromatobraphy on silica gel (methylene chloride/ methanol 40:1)

Sources & evidence

ORD record
ord-1134cea995b84f4c80db8ae02dbed89a
Source dataset
uspto-grants-2002_10
Patent number
US06462198B1

Reaction notes

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